Special Assignment
by Nidoran Duran
Summary: With the women of Konoha overly stressed, Shikamaru finds himself tasked by the Hokage herself with an unconventional means of helping people out after an offhand remark about how he handles his own stresses. Shikamaru/a lot of women. Anonymous commission.
1. Audition - Tsunade

Tsunade always reasoned that Shikamaru was the most mature of the young ninja in Konoha, that she could trust in him a certain level of composure and reliability, despite his intense laziness, which was her primary justification for handing him the glass of sake to go with her own. "You did well," she said, slipping him the drink as she leaned back in her chair. It was her treat for a mission well done once he'd been debriefed, a moment of connection and calm between the two. Perhaps not the most appropriate gesture for the Hokage to give toward a student, but she felt that he could handle it, and as a result shoved aside any concerns she may have had about giving him a little bit of alcohol. It was how she celebrated with plenty of adult ninjas, particular those closest to her, and there was a gesture in what she did that she found very important, signaling to the lazy genius what she saw in his future.

Slumped back in his chair on the opposite side of her desk, Shikamaru accepted the glass, and made note of sipping it slowly, so as not to tip her off to the fact he could handle his sake better than he should have; he didn't want to risk sinking Tsunade's offer of underage drinking by admitting to how much he'd done himself. "Thanks," he said with a nod, and watched as she showed much less restraint than he did by downing it all in one go, bringing it down quite hard onto the table and already pouring herself another one. With a shrug, Shikamaru downed the rest of it and placed his sake forward.

The Hokage gave him a wry smile, pouring the both of them each some more. "You're too young to drink like that," she noted, slamming back another glass of sake with the deserved defeatedness of someone who desperately needed the relief it sought. "And aside from your bad posture you don't seem like you need to drink like that, either." She leaned back and sighed, going for drink number three as she took a load off and sought to relax. Shikamaru had come back from his mission quite late, and she had no appointments after him that needed tending to, so she saw little reason not to relax. "Which is quite amazing, because every kunoichi I've seen today has been more tense than the last."

"What about the guys?" The stinging burn in his throat of the alcohol left him content with sipping at his second glass, relaxing and getting casual as he slipped into conversation with the Hokage. She was right; he didn't have anything to worry about, and could enjoy his drink at his leisure, something he sought to do as he unwound after his mission.

"Somehow, pretty relaxed. All the women in the village have more problems than they can handle and have been moody about it, but every man I've had to deal with today seemed at ease, even with everything on their plates."

"They must have gotten head before coming to visit you," Shikamaru muttered jokingly into his glass.

While he'd meant it as an off the cuff piece of wit, Tsunade's brows rose in thought and surprise. "Hmm," she mused, looking off to the side and thinking about what he'd said. "You might actually be on to something there." Another glass of sake splashed impatiently down her throat, and although she could take her liquor like a champ, she was getting just curious enough to lean forward, her arms pressing onto either side of her ample breasts to push them together, emphasizing her cleavage as she smiled toward him. "Elaborate."

His eyes very briefly flashed down, almost losing his sight into the deep valley of flesh between her massive tits, but he just barely got out, looking right up at her face. "It was a joke."

"Pretend it wasn't, for a minute."

"Well, when a guy's feeling tense, what does he do? If he can't have sex with someone, he'll just masturbate instead. He's feeling good, chemicals are released and his stress goes down, and he's able to deal with whatever's in front of him." All of this was purely hypothetical, but the more she seemed to take his explanation with awe and interest, the more he wondered if maybe she was letting that sake go to her head a little too easily. "So maybe, and we're still talking hypothetically here, the women of the village just need a good lay to help them sort their heads out."

"Remarkable," she mused, downing yet another glass of sake, feeling like she was teetering on the edge of an idea but needed just a little more push to get her there. "You know what, that's still a better theory than anything I've come up with. Maybe it's right, actually." She smirked, biting her lip as she eyed him a bit more appreciatively. "Hey, you're between missions now, right?"

"That's why I'm here," he said, narrowing his eyes a little, confused by where she was going, but guarded. She was hitting the sauce faster and faster, downing yet another sake as she leered at him, lips curling into a wide smile that worried him as much as it made his pants tighten; the beautiful and charming Tsunade looking at him so excitedly was something very few men in Konoha could react differently to.

"Excellent, because I think I may have another one for you. A special, secret assignment for right here in the village." She pushed her chair back, leaning against the back of her seat and smiling as she urged him forward. "Come sit in front of me, right on my desk. I have to see if you're 'equipped' for the task."

Shikamaru knew exactly what Tsunade meant by that, her subtlety having only dropped further and further with each new glass she downed, but he couldn't refuse such an offer. He stood up, almost embarrassed by the swell of his cock inside of his pants, the bulge quite visible as the sight of her cleavage and her come hither stare left him rock hard, but then, she wanted to see his dick, anyway, so he shoved any worries from his mind. He climbed onto the desk, urged by her with little hand motions and noises of agreement into the position she had in mind, one which saw him sitting on the edge of her desk, legs dangling off of it. She sat in front him, looking up with an excited glance as she licked her lips, and he felt the heat on him from it; her intention was obvious, but he was having a little trouble believing it.

"There aren't many boys I would trust with this mission," she said, biting her lip as she reached for his pants, the pronounced bulge large enough that she didn't even bother pretending she had to examine him before she'd give him his assignment. Her fingers traced along the outline, her approach one of assured, playful assertion as she made clear to the ninja who was in control, and who had the experience to justify that position. "But you might be perfect for the job. You're lazy, brilliant, and always have something to say, so you could certainly put that brain to work on helping people find solutions to their problems." She worked his pants off as he spoke, aggressively showing how much she desired the young ninja as she fished his cock out, eyes going wide in marvel at the long, thick cock standing to attention before her eyes. She wrapped her fingers tightly around it and give it a few strokes as she added, "And then you could this to work on calming them down."

As the beautiful older woman seized his cock and pumped it slowly, Shikamaru groaned, squirming a little on the edge of her desk. Her hand was warm and intensely soft, her grip expert and firm as she worked him over in a way that told him she knew exactly how to make him empty his balls in seconds flat if she wanted him to. "Not lazy enough to complain about this assignment," he noted, staring down at her. Between the angle he was looking down at her from and the fact she had his dick in her hand, he felt no shame about now staring much more appreciatively at her rack, at the deep cleavage that her top so eagerly flaunted. "Do I have the right equipment for the job?"

Tsunade's response was to reach for the obi around her waist, tugging on it and letting it come loose, which in turn made her blouse open up, revealing it to be open ends folded over one another and bound by the sash. A little roll of her shoulders helped slip it back, her ample breasts spilling forward, uncovered with the absence of a bra beneath her blouse, which left them exposed to Shikamaru's hungry eyes. "You certainly do." Her tongue dragged along her lips as she pondered what to do with his cock. It wasn't the biggest she'd ever seen, but nonetheless he was endowed enough that she doubted any woman in the village would have been disappointment if he was dispatched to 'help' her. Big enough that it was a lovely, rare treat she was eager to get some time in herself. "But just to be sure, I think we'll need to give you a test assignment first. I need to know that you have the skills and endurance for something like this; I want only the best for my kunoichi, after all."

She hooked her ankle under one of her chair's front legs, dragging it forward as she pushed herself toward Shikamaru, his position on her desk perfect for her to grab her massive breasts and drop them down into his lap, wrapping his cock in fleshy, soft warmth as she looked up at him, her bottom lip firmly between her teeth. There was no need to ask him if he wanted a titfuck, because she had yet to be with a man who didn't want his cock enveloped by her breasts; it was a given by that point that he would just want it, and the smile breaking across his face said that she had been right with yet another lucky man. It was a pleasure that no man seemed capable of turning down.

Shikamaru relaxed as she got to work, her breasts forming a tight, fleshy prison for his cock that dragged up and down the girthy member. The soft, plump skin of her fatty breasts rubbed electrically along his shaft, providing a sensation of warmth that he simply couldn't believe, even if it was everything he'd ever hoped it was. Tsunade's breasts were, predictably, quite the point of focus and excitement for anyone growing up in Konoha, the very attractive older woman simply irresistible and her rack quite legendary. And now he was indulging in the pleasures of her flesh, and could never brag about it to his friends. A horrible price, but one had had absolutely no problem with paying for something this good.

Rolling her nipples between her fingers, Tsunade sought to excite herself as she worked the young ninja over, her grip on her breasts steady. As foreplay, she adored giving titfucks, able to rile herself up as she worked the lucky cock before her over. Her breasts were intensely sensitive, and each throb of his cock flush between her breasts or squeeze she gave herself provided little jolts of pleasure that in short order had her thighs rubbing together. All the while, she kept her eyes pointed up toward him, providing lusty and somewhat tipsy glares as she focused on the pleasured expression creeping across his face, his cool demeanour slowly coming undone as she paid attention to his cock.

"Here is how I see it," she explained, voice a little deeper and breathier as she focused even more on her nipples. "When I send you on one of these 'assignments', you'll have two jobs. One will be to provide any general advice or direction to the woman about whatever problem she is handling. The other will to ensure she is sexually fulfilled and her head is clear. You're smart enough to do the former and certainly big enough for the latter, so I think we have something here. This will all be kept top secret, of course; that's a headache I don't need."

"Of course," Shikamaru said, nodding as he let a hand run through her soft hair, head leaning back to let out a groan as pre-cum leaked from his tip. "I wouldn't want to deal with all the attention that would get me." He couldn't believe that Tsunade was basically suggesting that she start pimping him out to needy women all over the village, but he could find nothing in that thought that he took any sort of issue with.

Content with what her breasts had done to rile him up, Tsunade next set her eyes on really showing him what she could do. She pulled her breasts back, which earned a groan from Shikamaru. Every man she pulled away from had the same reaction, the second half of which was a gasp of shock and arousal as she then leaned forward and practically swallowed their cocks whole. She took Shikamaru all the way into her mouth, pressed a needy kiss down to his base, and wrapped her lips tightly around them. His impressive cock wasn't taken down with perfect ease, a few gags spilling out of her throat as he stretched the lining of her throat out, not only providing a tightness that excited both of them, but getting a nice depth out of the oral penetration as well. Sasuke was bigger, but the Uchiha boy was missing in action, and the biggest she'd had recently was hardly an unwanted title.

But the choking noises didn't stop her for a second. Tsunade quickly got to work bobbing her head, proving that she could deepthroat him like a champ. One hand wrapped around his base, fingers pressing and massing his dangling, aching ball sac as her other hand sank down into her pants, her heated folds dripping from the arousal she'd built up, which now needed to be tended to. Two fingers sank quickly into her slick pussy, pumping desperately into her as she showed off her pent-up frustrations more clearly now for Shikamaru, her cocksucking growing frantic and desperate in pace within only seconds first tasting the salty pre upon her tongue.

It was a rather juvenile joke to take Tsunade's nickname of "Legendary Sucker" to imply things other than her terrible luck at gambling games, but one that nonetheless every boy made. Of course, feeling her mouth now, hot and wet around his cock, her head bobbing quickly and not only taking him without much trouble, but doing so with such vigour and speed proved to be his undoing, and she was certainly earning her title in more ways than one; this blowjob was truly nothing short of legendary. He groaned, hands holding tightly onto the edges of the desk as he witnessed the work of pure cocksucking art she was putting on for him. The feeling was unlike any other head he'd ever received, and it took everything he had not to just blow his load into her hot, thirsty mouth as saliva filled it up, providing a wet and slick experience. Not quite sloppy though; she was restrained, expertly managing all of the little elements and variables as she worked him over with her mouth.

Tsunade pumped her fingers deep into her needy twat, the bobbing of her head growing more and more feverish as her own arousal began to catch up with her. She was showing it rather clearly, moaning and soaking in every little noise and grunt Shikamaru made, and with each passing moment his own noises grew louder as she did him in, providing the young ninja with more pleasure than he could likely handle, and certainly more than he had ever known before. The fact he hadn't already blown his load just from the titfuck was admirable in her eyes; if he could handle her skilled touch, then girls like Ino or Tenten who lacked Tsunade's decades of sexual expertise

Which wasn't to say he wasn't close, of course. Shikamaru groaned as the tight vacuum seal around his cock, the clenching, slick throat and the tongue slithering around the lower portion of his shaft still in her mouth proper, all sought to do him in quickly. He knew he wouldn't last forever, that he was well on his way to losing himself in short order amid the flurry of sensations he was being bombarded by. Never before had he held back on cumming as hard as he was then, wanting to keep the amazing feeling of Tsunade deepthroating his cock rolling for as long as he physically could.

But his body wanted release, wanting to cash in the jackpot she'd been steadily feeding, and with a mighty groan of relief he finally gave in. He shuddered, hips bucking forward off the desk as he came, cum splashing down Tsunade's throat without warning and to the Hokage's surprise. She pulled back, letting the rest empty out into her mouth, which flooded with the salty, warm treat she found utterly delicious, making her eyes close halfway as she purred, savouring the heavy flavour of the virile sperm for a moment before she swallowed it all down.

She pulled up, shuddering and moaning as some pearly droplets ran down her chin. "Oh, you are definitely the right man for the job." As she came up, she went for a few things all at once. The hand down her panties quickly did away with anything she was wearing below the waist, discarding it all in a single, impatient motion, while her other hand grabbing Shikamaru by the shoulder, pushing him down onto the desk until he was supine and she was straddling him, her drooling pussy lips rubbing up the underside of his throbbing cock. "And now you can deal with your first assignment; me. I can't wait to see the pleasure on your cute face." She licked her lips, the alcohol having taken full effect by that point, leaving her rocking back and forth as she sank down onto Shikamaru's dick, took him all into her. "Oh, fuck!"

It scratched an itch she had let go on for far, far too long, moaning loudly as she felt the fullness of his thick shaft opening her up, granting her a reprieve from the lonely and dull routine she'd gotten into with her vibrator. There was a warmth to his cock spreading her open that just felt right, and in short order she was bouncing in his lap, her hands on his chest and holding tightly to the hem of his shirt as she rode him. There was a drunken, wicked smile painted across her lips as she moved, her breasts heaving and bouncing wildly from the eager, heavy motions of her body rising and falling atop his aching, turgid shaft.

Shikamaru lay beneath her with a shocked smile across his face. The intense tightness of her needy, clenching pussy as she leaked quim all over his lap was amazing and borderline unbearable in its sheer, overwhelming pleasure. A naked Tsunade was in his lap, her gorgeous body laid bare for his eyes as she relished in the pleasure of using his body, of asserting herself and dominantly riding out the twisted thrills she was after. Every last bit of motion before him was intense and worthy of deep appreciation as her body moved with a practiced and rawly sexual grace, a treat for his eyes as her hips rolled and her body swayed. All the while, her face was the one wracked in pleasure, proving herself even more consumed by arousal than she'd wanted him to be.

He could have laid there lazily and let Tsunade have her way with him, put in little effort as she showed her wild side and dominated him quite thoroughly, but a rare spark of effort came over him; he wanted to prove himself capable of both performing the job Tsunade had in mind for him, but also of being able to fuck the gorgeous blonde in a way that would leave her totally floored. The opportunity before him was once in a lifetime, and he couldn't in good conscience let it fly past him. No, he had to live up to the chance before him, prove himself in a way she would never have expected, and seize the bragging rights before him.

Grabbing two big handfuls of her plump ass, Shikamaru threw Tsunade off her gave as he pushed up, lifting her briefly before turning around and bringing her down to lie on her desk in his place. The older woman gasped as he moved her around, confused and about to complain about having her dominance challenged, when he pulled back and slammed deep into her. The thrust silenced her complaints, replaced them with a ragged cry of pleasure as he shoved himself balls deep into her. Not only did he fill her up, but he came in at the perfect angle to hit her g-spot, leaving her writhing on the table, breathless and in shock as he got to work. The lazy genius had suddenly thrown himself into overdrive, letting all of the backed up effort loose onto her needy and long-since neglected pussy, leaving her in shock at just how well he could fuck when he had a reason to.

Her breasts heaved and bounced from the force of his thrusts, and for someone so generally unwilling to do much of anything, he showed himself to be quite fierce in the bedroom. His pounding slams forward into her clenching, dripping pussy left both of them groaning as he squeezed her hips, holding tightly onto her for support, to keep her steady even as his hips came down hard against hers. "I guess this is finally an assignment I wouldn't mind putting my all into it," he smirked, cocky as he watched the Hokage moan and writhe before him, proving himself capable of fucking even the storied cougar until she was a quivering mess.

Tsunade was in shock, but the amazement at his skills dwarfed her surprise at his exertion. She was too busy crying out, grabbing the edges of her desk for stability as she lost herself. Each thrust seemed to hit her just right, his turgid head rubbing against her g-spot each time he entered her, the sweet friction doing her in so mercilessly fast that she didn't even mind that their roles had been so wickedly switched. No, there was no time to fret about such things when her orgasm tore through her, leaving her howling and shuddering, spine arching up as she lost herself. Her pussy clenched hungrily down around his cock, just in time to milk his own orgasm from him, leave his cock spurting a hot load deep inside of her that added to the warm sensation coursing through her body as her climax wore her down. The surging, white-hot bliss through her veins seemed to wash away all of the worries she'd had in a cathartic cleansing.

Shikamaru withdrew from inside of her, groaning and breathless as one last little strand of cum splattered along her inner thigh. "I'm looking forward to this assignment, now," he said, smiling as he fell back into Tsunade's chair. He really couldn't help but feel cocky about his accomplishment, about leaving Tsunade whining as his cum leaked out of her hole, his cock still rock hard after two orgasms clustered rather close together. It had been proof of his talents in a way he'd never thought he'd get to flaunt. "I think it's finally some work that I can really put my talents toward."

Tsunade rose slowly, purring and biting her lip as she looked at him. "It most certainly is," she smiled, leaning forward and looking pleased down at his still rigid shaft. "You're definitely the man for the job. You'll receive scrolls with your assignments when I have them, or be called into my office. The girls will be told to keep this secret as well."

"Why go by two forms of assigning my targets?"

"Because when I call you into my office, I'm your assignment." Pushing off of the desk, she climbed into his lap, her hand seizing his sticky, wet cock as she settled down happily atop him. "Who in Konoha could have more stress to work out than me?"


	2. Posture - Tenten

When Shikamaru received a scroll with his first assignment, he was a little disappointed, if only because he'd been hoping that Tsunade's promise that she would sometimes call him into her office meant that he could maybe angle for a little pre-mission relief of his own stresses with the gorgeous Hokage. Not that he was going to complain much about his task when he saw Tenten's name on the scroll; being tasked with helping and then subsequently 'helping' the adorable weapons master sounded like a great way to start off Shikamaru's new line of work. The scroll explained briefly her issue with a new weapon she had procured and her difficulty in figuring out how to use it properly. A simple task, one Shikamaru could even clear up before he cleared her head up afterward.

The only issue was in putting his book down to do it.

But once he had-and had gotten dressed-he went to go meet Tenten. The black-haired girl answered his knock on her door almost worryingly quickly, blushing more than a little as he arrived. She hid the shyness that the situation had no doubt induced behind a steady, confident mask, not wanting to appear weak or less stoic than the aloof ninja who had come to help her. "I'm glad you could make it," she said. "Please, come in. The training room is this way."

"The scroll said you were having problems with a weapon," Shikamaru said, following after her at a leisurely pace, mostly because with a little distance between the two, he could admire how her tight pants held to the firm, taut curve of her toned bottom, almost criminally tight. There were far too many gorgeous girls in his class for him to be a hundred percent certain who the hottest was, but with a bouncing view like that and the knowledge that Tenten knew what he was there for, she had certainly shot up in the ranking quite a bit. "And I was a little surprised to hear that. I thought you were a master with every wea-" He went silent as he stepped into the training room, amazed by the sheer scope of weaponry in front of him.

The training room held an assortment of targets and dummies, all stuck with a dizzying array of weapons. Lining the walls were racks containing kunais of all sizes, blades, fans, grenades, spears, blunt weapons... There was no doubt that her home was better stocked than the academy's armory, and within a few years would probably come to rival the city's. He looked around in awe, then back at a smiling Tenten.

"I thought you'd like that," she said. "But the problem is this." She strode toward a large red line drawn into the mats, numbers beside them indicating distance from the main target, a plank of wood with a human silhouette nailed to it. Arrows plunged into the target picture, but in a loose cluster that ran the gamut of penetrations. All of the shots hit the human outline, but none of them landed on the red circle over the heart. A very long bow lay over the line, and as Tenten pulled it up, she revealed that it was considerably taller than she was. "I'm used to crossbows, and I can't figure out how to fire it accurately. Which only has me too frustrated to train with any of my other weapons."

Shikamaru smiled as he looked at her holding the bow up; he'd only a week ago been reading up on proper archery form. Or rather, rereading; he had found a more comprehensive book on the subject than he'd previously read through, so the information was especially fresh in his mind. "I can help you with the bow. And with your other thing." He spoke so matter-of-factly, but he could still see the way she squirmed a little at the implication. They both knew what she had called him over for, that he was there to help the girls of the village with more than just advice, but it was an awkwardly unspoken thing as he walked closer toward her. "Draw an arrow and hold it, I'll check your posture."

The problem was immediately apparent as Tenten assumed the position, staring down the target fiercely. She stood awkwardly, holding the posture of someone throwing a weapon, whose body was ready to spring forward at a second's notice and add momentum to the attack. Most of all, her arm was utterly off center relative to the arrow. "I went with how I felt I should be doing it," she said, looking forward. "But I'm guessing it's not right."

"Not at all," Shikamaru said, stepping forward. His hands descended upon her arms and midsection, and he began to guide her into a proper position. "The bow does all of the work for you, so you want to keep your posture as straight as possible, otherwise you disrupt the shot. And for your arm, you want it to be aligned with the arrow itself." His body pressed up against hers, and as his hands ran along her bare arms and hips to straighten her out, she could feel something pressing against her rear end, something that she hadn't noticed before, perhaps for awkward fear of not wanting to look anywhere below the chest of her visitor. But now it was right up against her ass, a firm, rigid bulge that left her cheeks burning as he finished getting her ready. "There, that's better. Don't think about it like you're trying to throw something; stand straight, and the bow will shoot it for you. Try and fire it."

Tenten took a deep breath as she lined up her shot, keeping her body in the position Shikamaru had guided her to, and gently released the end of the arrow. It flew forward, sinking right into the small red circle on the target, the first shot she'd fired to fly true. Her chest swelled with pride and relief as she made her mark, instinctively pulling back a little to disengage and get another arrow, but that only led to pressing harder back against Shikamaru. Against his warmth and his embrace, and most damningly, her ass against his bulge. "Thanks," she said shakily, biting her lip as the relief cleared her mind and left her very aware of just how much bulge there was.

"Do you want to take a few more shots of your own to make sure you have it down?" Shikamaru asked, not pulling away from the girl as she pressed against him and indicated that she wanted something else entirely. "Or shou-"

Tenten was not a demure, helpless little damsel who was going to fret and blush until Shikamaru got on with it. Tsunade had told her exactly what kind of 'help' Shikamaru could offer her and she agreed to it. With the task now complete, she turned her attention toward the more pressing matter. As in, the matter pressing against her rear end. Shikamaru's question was cut off by her lips pushing against his, his back quickly finding nowhere else to go as the wall blocked his path and the excitable, somewhat sweaty Tenten pressed him tightly up against it. It was the answer to his question he didn't know he needed, a forward and surprisingly aggressive pouncing from Tenten. He met the kiss, his hands running down her back, moving quickly to her ass, boldly taking firm handfuls of it. The lazy genius's work ethic suddenly flared up quite intensely once he was given something he could really get invested in.

"Not here," she said, even as her hand ran through his hair and she pressed back into the heated kiss. "My room. Weapons aren't the only things I have too many of."

What could possibly have been meant by that was beyond Shikamaru, but he was eager to find out, pushing off of the wall in challenge of her aggression and urging her out of the training room. The two still grabbed and kissed frantically, moving slowly through the hallway and toward Tenten's bedroom, all the while utterly unable to keep their hands off each other. Shikamaru had one clinging tightly to the girl's ass the whole way there, until her back was against the bedroom door and it was his turn to do the pressing.

Finally, Tenten let go of Shikamaru, fumbling for the doorknob, and the way his body pressed against hers meant that they went stumbling into the room. It was entirely intentional, granting Tenten some much needed distance as she went for her dresser, opening up the cabinet inside to reveal a dizzying array of sex toys that were about as crammed in there as they could have been while still having a semblance of organization. "I like my toys, in combat and in the bedroom." She smiled, running her fingers along one as Shikamaru steadied his footing, decided eventually on a long, ridged and bumped purple dildo that she tossed toward Shikamaru. "And if you want this to work out, you're going to have to figure out how to use that on me."

Shikamaru caught it and gave it a quick look over, but it was disrupted only seconds later when Tenten bend over her bed, hooked her thumbs into her pants, and slid them down, revealing the lovely curve of her ass and the puffy pink pussy between her legs. She was unabashedly forward now about her desires, and unwilling to fall behind, Shikamaru descended upon her, deciding he'd figure out how to get the toy into her once he was able to satisfy his own urges. His pants were quickly done away with, his impressive cock tracing circles along her plump mound, feeling the wetness the little tease and make out session had provided, before he sank into her.

Tenten was crying out in relief before Shikamaru had even fully registered the sensation. "Nngh, that's perfect," she whined, hands reaching out toward the bunched up blankets in front of her as she pushed back a little against Shikamaru's lap. She'd spent plenty of time messing around with her collection of sex toys, mastered the use of them for her own needs, but there was something they couldn't provide that he could. Warmth. Realness. The facsimile of a cock was perfect for the raw physical sensation, but the emotional feeling of another's touch pushed over the edge her pursuit of pleasure, and she settled excitedly into whatever it was Shikamaru had in mind as she let him have the first round, eager to test him out.

The tight, dripping heat of Tenten's pussy around his shaft was exactly what Shikamaru had needed to relieve his own urges, bubbling up after tasting her lips. He got to thrusting quickly, the only job in the world he would put his all into, and savoured the way her vaginal walls clenched down, pulling his cock back in and lamenting his withdrawal. He leaned forward a little, standing over her and getting a good angle going by which to fuck the pent-up and frustrated girl, loving the way she was moaning so quickly. This wasn't like with Tsunade, where he had something to prove and she seemingly didn't want to give him a victory too quickly. Tenten was more than willing to vocalize how she felt, moaning and shuddering loudly, giving his ears the sweet and ego-boosting treat. "How long as it been?" he asked, his free hand fondling her bare ass as he ran the head of the dildo between the cheeks.

"Too long," she said, biting her lip as she turned back to look at him. "But you're hitting the spot perfectly. Don't stop doing that." Her fingers pushed into the bed a little, pressing needily against just about anything; she just needed to grab, and unlike most of her nights alone, she didn't have a sex toy to squeeze too tightly. It was an instinct that left her shuddering as he started to fuck her faster and faster, his hips building up a steady and intense pace, the kind that she needed. "Do you really think this is going to help my frustrations?"

"Of course," Shikamaru said, not entirely certain of anything, but he would have had to be an idiot to undersell his services while buried her pussy. "Guys use this to clear their heads all the time." The toy lined up with her adorable, pink pucker, wiggling against it and drawing the most adorable of moans from Tenten's lips before he sank it forward, slowly working it into her ass with a patient push as his hips continued to provide the lurid counterpoint of a hard fucking. His free hand squeezed her ass almost too tightly as he gave her holes the utterly contrasting approaches, but it didn't matter what he was doing to her so long as the moans continued, and she was becoming increasingly shameless about just how good his steady approach felt. His cock was opening her up and leaving her with the satisfaction she craved.

There was no reason not to believe Shikamaru about it. Not when he was tending so expertly to her needs, and Tenten surrendered to his assurance. "I don't have a lot of toys that are your size," she confessed, looking over at her open cabinet, at the embarrassing collection of dildos in all shapes and sizes, a dazzling array of colours, all adding up to an intense bout of shame. At least, it would have been shame, had Shikamaru not been beating out all of them. "So you can go even faster, I'm used to taking it." A little bit of shame did bubble up at the thought spilling from her lips next, but before she could think about if it was even worth saying, his cock bottomed out into her and she was crying it out anyway. "I-I really like it big. And rough, too."

Shikamaru's smile widened as he did exactly as the lady asked. His hips came crashing down into hers, filling the room quickly with the fleshy noises of their collision, of his cock rapidly sinking balls deep into her leaking snatch and her ass bouncing from each smack of his pelvis against them. The dildo in her ass not only sank in faster, but began to pump in and out, further stretching and preparing her tight back door for something else while adding to the immense pleasure crashing into her through Shikamaru's hung, warm cock spreading her pussy open in delight. Her moans came louder and faster, more ragged and endless as they overpowered Shikamaru's own; she was close, coming unwound desperately in front of him and losing herself to the shuddering, intense thrills of a long needed and much deserved pounding.

Soon, the dildo was working its way in and out just as hard and fast as his cock was, a double ended assault that left Tenten screaming in ecstasy, her orgasm hitting her hard, leaving her shuddering and writhing on the bed as she came. Her pussy leaked messily all over her bed and down Shikamaru's balls, a sense of cathartic relief washing over her as her frustrations began to melt away at long last. The searing, heated bliss through her body was only an added bonus as she went limp and still for a moment, but her lip as her head lay on the bed. The increased tightness of her vaginal walls attempting to close around the girthy intruder sent Shikamaru spilling out after her, his cock erupting and flooding her sloppy pussy with all of the hot spunk she needed to come down from her high excitedly.

But Tenten wasn't the kind of girl who basked in the afterglow. Crawling forward, she got off of his cock, reaching quickly for his collar and pulling him down onto the bed. "I wanted to see what you could do," she explained as she settled him down onto his back and pulled the embedded dildo from her ass. "I'm usually a lot more active in the bedroom, but you're kind of lazy, and I didn't know if that meant you were going to let me do all the work. Now that I know that's not the case..." She bit her lip, climbing into his lap and grabbing hold of his still rigid, throbbing cock. She lined it up with her slightly opened ass hole, her nectar providing a thick lubricative coating that she hoped would make it all smooth sailing. "Let's go crazy together."

Shikamaru's hands were quickly upon her hips. "Of course," he said, smiling as he watched her bring the dildo around front to where her pussy drooled out a sticky, lewd mixture of quim and his slowly seeping outward cum. She let a little bit of it ooze down onto the toy before she pushed it an inch deep into her hole and rocked back and downward, taking him slowly into her. "This feels even tighter," he groaned as her taut ass clung like a vice around the head of his cock. "But you want it hard."

"Don't give me anything less."

Rather than Tenten just sinking down onto the rest of his cock, or Shikamaru just thrusting upward, the two ninja met in the middle, both eagerly seeking the pleasure they wanted a second round of, and both more than willing to work for their release. They moaned in unison as their bodies got to work, wasting absolutely no time in fucking like rabbits, her ass quickly opening up even further as his thick cock hit her just hit, leaving her with a sense of fullness that she couldn't believe. The fake cock slipped into her pussy and Tenten began to madly fuck herself in Shikamaru's lap, giving the usually lazy genius the hot view of her masturbating while she bounced on his cock. It was impatient and frantic, and he was all too happy to slam up into her, his balls swinging upward and smacking against her toned cheeks as he stared in awe at just how hot she was.

Shikamaru had just been working the toy in and out of her ass, but much as she was a master of weaponry, Tenten used her dildo like an instrument she knew how to play perfectly, putting a brilliant performance on for her classmate. Her fingers held tightly to the toy as each ridge and bump along the thick shaft massaged her already slick, lingeringly sensitive vaginal walls, moving about so that on the way in the tip of it would hit her g-spot just right. There was a sense of pure artistry in how she moved, one that fascinated Shikamaru as he took notes, both for future reference and just so that he never forgot the sight of Tenten fucking herself for their mutual enjoyment. He understood why sex toys were something she was so insistent on, if she could do such amazing things to herself. Perhaps the warm touch of another was all she needed, as masturbation was clearly not unfulfilling for her.

"Faster," she moaned, rolling her head back and biting down on her lip. "I haven't felt this good in forever." It was a compliment of the highest order and Shikamaru knew it; she was putting on a show for him after all, but even her formidable masturbatory techniques were unable to dwarf the sensation of him fucking her, and it inspired him to work harder. To make more of those hot, intense moans spill from her lips. She was leaking all over him, her pussy dripping its sticky juices onto him, drooling as the toy fucked her harder, and he was ready to be made as big a mess as she wanted him to be if it meant this kept going.

One of his hands left her hip, reaching for her chest as, contained in her top and the bra beneath her breasts heaved in unison. His fingers undid the buttons of her blouse, opening it up and pulling her bra down so that he could get to one her breasts, certainly not the size of Tsunade's but far from insignificant. He fondled it, thumb and forefinger working her nipple over as the other fingers just pressed into the plump flesh, and the added layer of sensation made her spine arch back, her moans growing even louder as he added more of his hot touch. What a touch it was.

Their bodies moved in frantic unison, perfectly working together to reach their intense release together as they fell into a flawless, synchronized rhythm. In truth, Shikamaru was just very good at reading body language, at picking up Tenten's frantic pace as she subjected herself to the quick, intense double ended assault of his cock and her dildo, and was able to match that cadence with his own performance, ensuring that each time their bodies met together, it was absolutely perfect. The effort paid off quickly, Tenten's voice low and hot, and he couldn't get enough of it. Of her trembling moans and the way her body writhed as the simultaneous sex and masturbation turned into a lewd dance. She swayed and rolled and performed for his hungry eyes, all of her deadly grace rising to the surface as she showed just what she could do.

The closer she drew to her second release, the more Tenten understood just how much sex could have eased her troubled mind. Even when she wasn't actively sexually frustrated, somewhere in the back of her mind, she was. This was clearing all of that away, freeing her entire consciousness up for the task at hand, settling her nerves by giving them an intense and sweet indulgence so that they played nice. She wanted more of it, greedily bouncing faster on Shikamaru's glorious cock as she shouted at him to fuck her harder in turn. And he did, his hand squeezing her tit even tighter as he gave her what she wanted, and she hated that Shikamaru was doing this as an assigned role in the village, because she wanted to keep him on hand to fuck her tension out of her around the clock.

Being utterly filled ensured that Tenten beat Shikamaru to their second orgasms as well. She screamed as she hit her peak, her body even more worn down this time as greater pleasure tore through her, left her burning up and blushing and spinning madly out of control. Her dance became wild and unfettered, a performance given utterly to the careless procession of need and lust. She shoved the toy as deep into her as it could go with her grip still on it as she pressed down against his lap, sheating his cock into her and refusing to abate as she hit her climax feeling as full as could be. Her pussy gushed this time, a squirting orgasm that left a small spray of her nectar splattered on his chest.

There was no way Shikamaru couldn't follow that up with his own climax, and he came deep into her ass, grunting as her anal walls pulsated around his shaft all the while. Each hot spurt left Tenten purring deeper and louder as she writhed in the afterglow, momentarily taken off of her game by the amazing sensations. Shikamaru stared at the ragged girl in his lap as the last little spurt fired off into her, soaking in the sight of her after going over the edge. She was gorgeous in ways he really should have realized sooner, and it was the moment where everything about his job clicked for him. She was going to be far from the only one, wasn't she?

"Mm, that was amazing," she moaned, flopping downward and lazily seizing a slow kiss from Shikamaru. "I didn't actually think I needed that; I just needed the excuse to get you here. I uh. I kind of always wondered how you'd be in bed. The fact it's clearing my head is just a bonus."

"Did I do as well as you hoped?" Shikamaru asked, as though the answer wasn't blatantly obvious.

"Better. You don't have to leave, do you? Can you stay the night?'

"I can probably do you a bit better than that. I can stay until my next assignment."


	3. Scratching the Itch - Anko and Kurenai

Shikamaru almost did a doubletake when he looked at the scroll carrying his next mission; Anko. The loud kunoichi was a beautiful woman and Shikamaru could hardly process the idea that she would want to enlist his services for anything. And yet, that was precisely what he saw before him. There was no problem specified that he would be tasked with dealing with, which he found a little odd, but perhaps Tsunade had decided to pimp him out to women looking for resolutions only of more physical problems; he quite hadn't been clear on whether he was available for purely sexual services or not. And any time he tried to broach the topic to Tsunade, she seemed to obfuscate her answer by pulling him close and hiding him beneath her desk to service her.

Curious as to what she could have wanted, he headed off to Anko's apartment, admittedly a little more excited about this assignment than he'd been about Tenten, solely because of the immense compliment of a gorgeous ninja seeking his services when she could have no doubt had her pick of men in Konoha. The openness of the assignment and the lack of some mundane issue needing him to use the 'wrong' head only furthered his excitement, and he was all too ready to see where this went.

Until her front door opened, and Kurenai answered.

"Shikamaru?" she asked, clearly not having expected the younger ninja. "Anko, you said more food was being delivered." She turned back toward the woman of the house, who had sent her guest to answer the door knowing full well that there was no food coming.

"I lied," Anko replied glibly, smiling as she slid up behind her friend. "Please, come in. I've been expecting you."

Kurenai pulled away from the doorway and allowed shikamaru to come in, looking with confusion at Anko. Shikamaru joined her in shooting inquisitive looks toward the kunoichi, both of them wondering what was going on and what she had been planning, if there indeed was some kind of trickery afoot. Neither were fully certain what was happening, and her wry smile seemed to leave them only more confused.

"Anko?" Kurenai asked, looking in worry at Shikamaru, then back to her friend.

Knowing she couldn't keep this fun going forever, Anko came clean. "Do you remember the rumour that Tsunade had assigned one of the younger boys in the village to 'take care' of the women?" Her lips lifted off her teeth and into a wider smile as she walked past a stunned Kurenai, the realization dawning upon her in a mix of shock and outrage that only worsened as Anko sidled up beside Shikamaru, wrapping an arm around his waist from the side and pulling him in close. "Well, it's real, and he's right in front of you." Pecking a baffled Shikamaru on the cheek, she leaned in even closer, pressing her body against his. "Sorry I didn't leave any explanation, I wanted this to be a surprise for Kurenai."

"She's my mission?" he asked, catching on much quicker than the confused team leader. He hardly minded, eyes appraising the gorgeous mother; her body was incredible, and as far as beautiful women of Konoha went she was very high up on the list.

"Consider both of us your mission, but Kurenai even more."

"This isn't funny," she said, staring in disbelief at her friend, unable to process fully what was happening before her.

Anko shrugged. "I'm not laughing. You haven't been with somebody since Asuma passed away, and you're pent up. You need this. Besides..." She slipped behind Shikamaru and smirked, grabbing his pants and tugging them down. Her other hand ran grabbed his head, pressing it into her cleavage as she ran her fingers along his rather lengthly cock, slowly reaching the tip and giving it a tight grip. She pointed him directly at a stunned Kurenai as she began to slowly stroke his shaft, wasting absolutely no time in getting down to business and indulging in what she was after. Shikamaru offered up little resistance, shuddering as he felt the skilled hand work his cock over, Anko so skilled it came almost as a surprise.

Shikamaru pressed back against the woman's body, taut and warm and just a delight to feel against him as she reached around for his cock. Her slow stroking made pre ooze from his aching tip as his entire length was put on display for Kurenai, who for all her visible uncertainty couldn't take her eyes off of it, letting him know just how impressive she found it to be. She stood silent, the conflict visible upon her face, a stunned layer of fixation underneath that fueled the growing thoughts of arousal and curiosity, the temptation to indulge. It was a heavy conflict, especially as Anko's words of 'concern' echoed within her minds, leaving her feeling like maybe there was some truth to the idea.

"Come on, look at how big he is," Anko said playfully, gladly stroking the younger ninja's cock and wringing from pre from his tip. "Think about the fun we're going to have together. This is going to be so much better than tea and you know it." She kissed at Shikamaru's neck as she spoke, staring lustily toward her friend. "Let's enjoy the night instead of worrying about everything, okay? I did this so we could have some fun together."

Kurenai nodded, stepping forward, still utterly uncertain about this, but unable to resist the sight any longer, the way her friend's eyes were wide with excitement and arousal. "Okay," she said, nodding nervously, overcompensating with feigned confidence as she strode toward the other two. "We'll do this together, then."

Shikamaru was almost surprised how quickly the women began to move once Kurenai agreed to things. Anko did away with her friend's clothes before peeling her own mesh outfit off of her incredibly taut body. The woman of the house then led both of her guests by the hand to her bedroom, pushing Shikamaru down onto it and guiding Kurenai impatiently into the position she wanted, the one she'd had in mind for them to start with ever since she found out about this amazing service. Which was to say, Anko and Kurenai lying on their stomachs and coming in from the side, laying their breasts in unison over the lap of their entertainment, wrapping his thick cock around their ample cleavage and smiling at one another as they got to work.

They began to lift upward, dragging their breasts along his cock, treating Shikamaru to a double titfuck. Kurenai still had a lingering sense of uncertainty, but Anko's energy and forwardness was rather infectious, and she hardly wanted to be left behind, to be the one slacking off in this threesome and leaving Shikamaru feeling disappointed. She got to work, matching Anko's pace as she bit her lip, looking over to the ninja lying on his back, and what she saw back was a lusty, appreciative look appraising both women, and she had to say, it left her feeling almost young again. Kurenai couldn't put it into words, but after paying so little attention to men around her for so long, to be suddenly aware of how someone was looking at her like the beautiful woman that she was left her feeling more excited than she ever would have imagined.

Reaching down toward them, Shikamaru ran his hands through the soft hair of both women as their own hands remained firmly on their breasts. "This feels great," he groaned, very much aware of the need to make sure Kurenai felt good as he eased her down with compliments into comfort with the moment. He wanted to ensure that everyone was feeling good, and Kurenai was currently the one who needed that help. Just because his task was purely sexual didn't mean there wasn't a problem that needed solving. He caressed their hair as he watched them go, occasionally twisting a little bit in delight as he watched them smile back at him. And to each other.

Anko pressed her nipples against Kurenai's, drawing little moans from her friend as she started angling toward a little attention being paid between the women. "I told you this would be fun," she purred, biting her lip as she held her breasts tightly together, the fronts of their tits squished together as they rocked up and down against roughly half of his cock each. Neither women was legendarily busty, but combined, they were able to envelop his needy cock in enough warm, soft tit flesh to leave him feeling rather satisfied with the moment.

"You were right," Kurenai said, smiling back at her as she focused on the up and down motion, on marveling at the throbbing tip of Shikamaru's cock poking out from between their cleavage. It twitched quite regularly, dripping pre down that made their cleavage slicker, helped with the steady dragging of her tits along his shaft. She and Anko quickly fell into a nice pace, working in unison on him and keeping principled in their approach, even if arousal was starting to build a bit more for the team leader. Arousal like she had not felt in a long time. Far, far too long a time, in hindsight. "I may have needed this after all, thanks for doing this. You're a good friend."

Watching the two beautiful women talking as they gave him a double titfuck, Shikamaru couldn't help but get a little playful with the moment, easing their heads slowly forward. Both sets of eyes briefly turned toward him, but smiles crept across lips as they decided to play along, lips parting and meeting in the middle, the two women sharing a deep kiss together over his cock as their fingers slid forward, tracing places with the other. Kurenai and Anko grabbed hold of the other's breasts, squeezing them a little as they pressed them more firmly around his cock and picked the pace up a little, starting to revel a bit more in the touch and proximity of the other. The warmth and softness of another woman's breasts against theirs, of gentle lips and a tender, deep kiss as fingertips pressed into their own soft skin and in turn they felt the squish of tender breasts beneath their own tips.

"You just wanted an excuse to be with me, didn't you?" Kurenai hummed softly into Anko's mouth as her bottom lip was gently bit down on. "I don't mind, but you could have just said something." She laughed softly, rather absorbed in the moment and savouring the fun that was to be had. Her worries had quickly subsided, between the taste and touch of her dear friend, and the slow roll of Shikamaru's hips beginning to feed more quickness and friction into the titfuck.

She never got an answer to that question, as Shikamaru's cock quite suddenly throbbed in the tight warmth of their joined breasts. His cock erupted, quickly gushing forward with spurts of hot, pearly seed that left both girls gasping and pulling away as the first shot splattered right onto their chins. Leaning back, they moaned as they watched him loose the rest of his load, spurts of seed falling down and leaving their breasts streaked with long ropes of seed. Both of them shivered as they watched, biting their lips and feeling their lust reach higher peaks as they adored the sight before them. Neither had a single complaint about the virile display of the younger ninja's penis, but both of them were feeling more and more impatient by the second about finally getting some action.

"That was amazing," Shikamaru said, panting a little as he lay there, greeted with the amazing sight of Anko leaning boldly forward and licking the cum right off of Kurenai's cheek, trailing her tongue up to her lips and kissing her for a moment before angling her head back and allowing her friend to do the same. The lusty display that followed as their lips met again and they began to swap his cum back and forth in their sloppy kiss ensured that his cock wasn't going to soften one iota as he lay there. "But now, it's time to do what I came here to do. You've both been very kind to give me this first, but I have a mission to complete."

Anko purred, nodding as she remembered that this was still supposed to be about getting Kurenai laid, and her approach to helping further that was to pounce forward, driving the slightly bustier woman down onto the bed and lying atop her, both of them fully naked and eager for more. "I hope you're not the kind of man who has to kiss a girl he makes love to, because I'm taking her lips over," she said, running fingers softly along Kurenai's cheek as she looked back to Shikamaru, who remained utterly stunned by the display of intense, raw sexuality Anko was putting on for him. Nodding, he pulled himself up, the frantic exam proctor proving an impatient wildcard who moved gracelessly from one thing to another so quickly he was left almost a little shocked by it all. She was so incredibly loud and excitable, a stark contrast to Tsunade's confident dominance or Tenten's physicality tempered with desire. Not that he minded too much, of course, kneeling down behind the two girls whose tight bodies formed a rather lovely stack he intended to savour.

Cock in hand, he guided himself right into Kurenai's snatch, and mindful of how long it had been for her, he decided she needed a slow and steady lovemaking. He eased gently forward, his thick cock sinking slowly into the team leader, who moaned as Anko peppered her neck and cheek with a flurry of rapid kisses. The sound she made was a low, rumbling one, of an itch being scratched after years, leaving her utterly elated as she twisted a little beneath the weight atop her. And Shikamaru could most definitely feel why there was a need for his services; Kurenai was incredibly tight, save for perhaps some time with her fingers having received none of the sorely needed sexual attention the gorgeous woman deserved. He understood why, of course, and took his duty seriously as he sought to tend to her long burning needs.

Slow thrusts rocked in and out of Kurenai steadily, leaving her twisting in delight. She hadn't been thinking much about her sexual needs until Anko had brought them up, but Shikamaru was not only bringing them up to the surface, he was tending to them, a problem solving itself the moment it came up, and the eager hands grabbing at her breasts and lips against hers made her feel like she had a longer-lasting solution to those woes in the form of the eager woman lying atop her. She hardly minded the prospect, but for the moment, she was more taken by the feeling of fullness that Shikamaru brought. She moaned into the deep kisses being laid upon her lips, her own hands wrapping tightly to Anko, clinging needily to her as she was taken. It felt like heaven.

"Too long," she purred. "Oh, it's been too long. Deeper, Shikamaru, please. I want to feel full again." She gasped, head rolling back, pressing into the pillow as her neck was assaulted once more. Shikamaru's thrusts were deep and steady, tempered with finesse and an expert touch as his hands ran along her outer thighs, kept her legs from entangling too much into a mess with Anko's. His sexual prowess was immense, and she could hardly believe how much the young ninja was hitting the spot just right, certainly possessing more than size as his steady, skilled thrusts hit her perfectly, not that the long, thick cock throbbing inside of her needy snatch wasn't also excellent.

Watching the two women go at it, Shikamaru felt like the luckiest guy in Konoha for landing this gig. His hips rolled steadily, sinking time and again into the slick heat of Kurenai's pussy, which clung needily to his cock and refused to let it go. He was on cloud nine, elated as he moved steadily, taking her deep and with enough passion to keep her from losing the spark of heavy lust within her; she was not in a state where she needed anything intense on a physical level. Emotional intensity was a given, and Anko provided that in droves as she made out with her, grabbing at her body with a recklessness that held more passion than the usual aimlessly frenetic energy she approached things with. Ir was constructive and directed, mixing well with the loving touch of Shikamaru and his steady, principled thrusts, overwhelming the widow with sensation and affection that left her twisting and writhing in excited, heated bliss on Anko's queen size bed.

Quickly turning into a dripping, moaning mess, Kurenai grabbed at Anko's back, squirming on the bed as she soaked in all of the attention and affection. It was amazing, leaving her utterly satisfied before she'd even hit her peak; there was just something so sweet and infectious about their combined attention, about their efforts to satisfy her neglected sexual needs. It warmed her over to feel so loved and taken care of, pushed to the gasping edge by two people who treated her with the tenderness she needed to be coaxed back into the realm of sex after all this time. Their touch was so loving and gentle that she gladly sank down into the deepest depths of her need and arousal, trembling as she felt herself go over the edge.

The first orgasm another's touch had brought her in years sent moans spilling needily from Kurenai's lips, and Anko could feel the vibrations rumbling in her throat as she kissed all over her neck, sucking gently at it as her hands founds Kurenai's and held tightly onto them. Her vaginal walls clenched and spasmed, that last extra push Shikamaru needed to follow her as he spilled over the edge himself, filling her needy, trembling pussy with a hot spurt of thick, much needed seed that seemed to satisfy another appetite she had pushed so far from her awareness that she was only aware of it as it was being tended. She trembled and shook as they went over the edge together, both falling limp and breathless for a moment.

Anko thought it was time for a break, that Shikamaru would need some rest and perhaps something to drink before she asked him about tending to her own needs, but she felt his cock slip out of Kurenai and tease along her own dripping, puffy mound well before she even thought it was 'polite' to begin asking about her own orgasm, and it made her tighten up in excitement. "Oh," she purred, leaning up form her friend's lips to look over her shoulder. "I wasn't expecting you take the initiative."

There was no way of telling Anko how much he'd wanted to fuck her since he first took his chunin exam that wouldn't put a damper on the moment, so he sought to show her with actions instead. Pushing forward, he showed off his versatility and grasp on somebody's sexual desires by pushing her into markedly faster than he had Kurenai, and got immediately to pounding the exam proctor furiously. Anko's energy meant that there was no way she'd be happy with a slow and passionate bout of fucking like he'd given Kurenai; she needed it rough and fast, and he was all too happy to oblige in hammering the loud woman until she no longer had the breath to cry out.

Kurenai stared in awe at the sight of Anko getting fucked senseless above her, eyes wide and rolled back a little, lip firmly between teeth. She leaned up, returning the favour by going at her friend's neck, hands advancing and seizing her breasts. While Anko hadn't fully acclimated to Kurenai's need for slowness, the inverse was hardly as true; Kurenai knew what Anko needed as well, and her touch was firm and aggressive as she fondled the moaning woman, nibbling at her neck and collarbone excitedly as she worked, pressing her body up against the woman keeping her pinned to the bed. With Shikamaru leaning down a little to get a better angle, Anko ended up sandwiched between two strong bodies of the people most eager to pleasure her in that moment, and the moans that followed were frantic signs of how much she adored it.

The force of Shikamaru's hard thrusts made his balls swing forward and smack against Kurenai's mound as it leaked with his seed, and she rather liked the little rough edge it added, the way that Anko was getting fucked so hard that some of the aggression splashed over to strike her. She reveled in it, using it to fuel the way she fondled and bit at Anko's neck. Shikamaru's hands gripped firmly at Anko's hips, making sure both women he had been tasked with pleasuring-in this case, the one he'd actually been asigned to-were more than happy with the results of his work. He pounded the dripping, clenching snatch that needily clung to his cock and leaked down onto Kurenai's, the fleshy slapping noises that filled the room utterly drowned out by Anko's cries no matter how hard he fucked her. She was unable to stop being loud, but neither of her partners would even consider asking her to quiet down, adoring the way she was so completely gone.

"No wonder you got the job," Anko cried out, hands wrapped tightly around Kurenai as she embraced being sandwiched and lavished with speedy, aggressive affection. Shikamaru's hips crashing down against her taut ass time and again was a feeling she should not have gone this long without, and perhaps she was a little too selfless about enlisting his services for Kurenai's sake; she would need a night with only him at some point, to be the sole focal point of his sexual talents for a night. She was certain Kurenai had the exact same thing in mind, of course; both women were more than glad to indulge in the hot, heavy threesome with him, but both were already figuring out when they could try and angle for him to service them and them only. "Hngh, fuck!"

Kurenai pressed her lower body tightly up against Anko, grinding their clits together as she savoured the raw friction of Shikamaru's cock grinding along her mound as it pistoned rapidly in and out of Anko's. Only one orgasm into the dual tenderness and she already felt like she had eyes for something a little rougher, but there wasn't a single shred of regret felt as she rolled with the amazing sensations. Hearing the sounds of the fleshy slapping and seeing the way Anko burned in delight, she rather felt like it was time to ramp things up on her end, too.

Not that it was the time for that; this was Anko's moment, and oh what a moment it was. The lady of the house screamed as she came, searing and intense pleasure running hot through her veins, leaving her howling as she pushed down aggressively against Kurenai, pinning her down and making out furiously with her friend, whom she sought to be something 'more' with. Her orgasm was powerful and draining, both of her energy and the contents of Shikamaru's balls as the male ninja blew his load into her clenching, sopping wet hole, topping her off with a creampie just like he had Kurenai, the two of them briefly shivering in delight against one another before Shikamaru found himself leaning down atop the two kissing women.

Their bodies disentangled quickly, but only so Anko could pull Shikamaru down into the kiss, turning it into a sloppy three-way mess of tongues and lips. Shikamaru felt that on some level, he'd accomplished something, expected or not, in giving Anko the platform needed to help coax Kurenai into a relationship with her. The task had not been one of pure sex after all, leaving him feeling accomplished as the two women wrapped their arms around him and held him close; the women may have been slipping further and further toward something emotional together, but for the night, he was the star of their bed, and they were not going to leave him out.


End file.
